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2,3-DMA; 2,3-Dimethoxyamphetamine
2162
Variant: N α R2 R3 R4 R5 R6 R2,3 skeleton isomers all
Analogues: 1 2 1 4 5 4 5 7 2 45 76

IUPAC: 1-(2,3-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: DHLWJXGSZDJWKK-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3

PubChem CID: 91255; ChemSpider: 82404

Shulgin Index: #34 2,3-DMA; Table: 4 Page: 325 Row: 30

See also PiHKAL: #55 3,4-DMA #124 META-DOB    

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

One N analogue:
6381
Analogue 1: Adding Methyl at N

N-Me-2,3-DMA

IUPAC: 1-(2,3-Dimethoxyphenyl)-N-methylpropan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: KJHJIEUXRKAETR-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-9(13-2)8-10-6-5-7-11(14-3)12(10)15-4/h5-7,9,13H,8H2,1-4H3

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 31

Clark, CC. The identification of methoxy-N-methylamphetamines. J. Forensic Sci., 1 Oct 1984, 29 (4), 1056–1071. 423 kB. doi:10.1520/JFS11772J

Two α analogues:
448
Analogue 1: Removing Methyl at α

2,3-DMPEA

IUPAC: 2-(2,3-Dimethoxyphenyl)ethan-1-amine

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: XKBUFTXNLBWTFP-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-12-9-5-3-4-8(6-7-11)10(9)13-2/h3-5H,6-7,11H2,1-2H3

PubChem CID: 137858; ChemSpider: 121507

Shulgin Index: #46 2,3-DMPEA; Table: 4 Page: 325 Row: 27

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. doi:10.1021/jm00327a016

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on dimethoxyphenethylamines (DMPEA): Regioisomers related to 2,5-DMPEA. J. Chromatogr. Sci., 1 Jan 2012, 50 (1), 1–9. 594 kB. doi:10.1093/chromsci/bmr013

6401
Analogue 2: Substituting Ethyl for Methyl at α

4C-2,3-DMPEA

IUPAC: 1-(2,3-Dimethoxyphenyl)-N-methylbutan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: VZITXQDEJMXSLF-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-11(14-2)9-10-7-6-8-12(15-3)13(10)16-4/h6-8,11,14H,5,9H2,1-4H3

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 326 Row: 1

One R2 analogue:
268
Analogue 1: Removing Methoxy at R2

3-MA
MMA (3-MA)
3-Methoxyamphetamine

IUPAC: 1-(3-Methoxyphenyl)propan-2-amine

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: VEJWNIYARKAHFI-UHFFFAOYSA-N

InChI=1S/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3

PubChem CID: 152234; ChemSpider: 134180; Wikipedia: 3-Methoxyamphetamine

Shulgin Index: #75 3-MA; Table: 3 Page: 321 Row: 26

See also PiHKAL: #97 4-MA      

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 2618 kB.

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., 1971, 54 (5), 1179–1191. 3851 kB.

Foster, BC; Litster, DL; Lodge, BA. Biotransformation of 2-, 3-, and 4-methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1991, 21 (10), 1337–1346. 553 kB. doi:10.3109/00498259109043208

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Four R3 analogues:
267
Analogue 1: Removing Methoxy at R3

2-MA
OMA
2-Methoxyamphetamine

IUPAC: 1-(2-Methoxyphenyl)propan-2-amine

Formula: C10H15NO Molecular weight: 165.2322 g/mol InChI Key: VBAHFEPKESUPDE-UHFFFAOYSA-N

InChI=1S/C10H15NO/c1-8(11)7-9-5-3-4-6-10(9)12-2/h3-6,8H,7,11H2,1-2H3

PubChem CID: 159755; ChemSpider: 140465

Shulgin Index: #74 2-MA; Table: 3 Page: 320 Row: 1

See also PiHKAL: #97 4-MA      

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

Foster, BC; Litster, DL; Lodge, BA. Biotransformation of 2-, 3-, and 4-methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1991, 21 (10), 1337–1346. 553 kB. doi:10.3109/00498259109043208

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 2002, 48 (1), 14–21. 181 kB. doi:10.1248/jhs.48.14

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Dal Cason, TA. A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Forensic Sci. Int., 1 Jan 2001, 119 (3), 168–194. 678 kB. doi:10.1016/S0379-0738(00)00425-4

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Bailey, K; Beckstead, HD; Legault, D; Verner, D. Identification of 2-, 3-, and 4-methoxyamphetamines and 2-, 3-, and 4-methylamphetamines. J. Assoc. Off. Anal. Chem., 1974, 57 (5), 1134–1143. 2618 kB.

6369
Analogue 2: Substituting Methyl for Methoxy at R3

2,3-MMeA

IUPAC: 1-(2-Methoxy-3-methylphenyl)propan-2-amine

Formula: C11H17NO Molecular weight: 179.25878 g/mol InChI Key: WWGNFBZBLDQURC-UHFFFAOYSA-N

InChI=1S/C11H17NO/c1-8-5-4-6-10(7-9(2)12)11(8)13-3/h4-6,9H,7,12H2,1-3H3

PubChem CID: 3029797; ChemSpider: 2295070

Shulgin Index: See #34 2,3-DMA; Table: 4 Page: 325 Row: 19

2762
Analogue 3: Substituting Hydroxy for Methoxy at R3

IUPAC: 3-(2-Aminopropyl)-2-methoxyphenol

Formula: C10H15NO2 Molecular weight: 181.2316 g/mol InChI Key: PKIJOVMSOHJKHU-UHFFFAOYSA-N

InChI=1S/C10H15NO2/c1-7(11)6-8-4-3-5-9(12)10(8)13-2/h3-5,7,12H,6,11H2,1-2H3

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

2760
Analogue 4: Substituting Hydroxy for Methoxy at R3

IUPAC: 2-Methoxy-3-[2-(methylamino)propyl]phenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: IUYNSRBNRQIZHF-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12-2)7-9-5-4-6-10(13)11(9)14-3/h4-6,8,12-13H,7H2,1-3H3

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

Five R4 analogues:
159
Analogue 1: Adding Methoxy at R4

TMA-3
2,3,4-Trimethoxyamphetamine

IUPAC: 1-(2,3,4-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: LWDQPPLPHGXYLG-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31012; ChemSpider: 28771; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #119 TMA-3; Table: 5 Page: 338 Row: 15

See also PiHKAL: #42 Ψ-2C-T-4 #152 2-TIM #158 TMA-2  
See also Pharmacology notes I: p. 72, SARs
p. 85.1, Subacute evaluation TMA-3 (XVI-13)

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

2334
Analogue 2: Adding Phenylpropyl at R4

2,3-Dimethoxy-4-phenylpropylamphetamine

IUPAC: 1-[2,3-Dimethoxy-4-(3-phenylpropyl)phenyl]propan-2-amine

Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: KCLVWBXTFNWCNT-UHFFFAOYSA-N

InChI=1S/C20H27NO2/c1-15(21)14-18-13-12-17(19(22-2)20(18)23-3)11-7-10-16-8-5-4-6-9-16/h4-6,8-9,12-13,15H,7,10-11,14,21H2,1-3H3

PubChem CID: 10403321; ChemSpider: 8578759

Dowd, CS; Herrick-Davis, K; Egan, C; DuPre, A; Smith, C; Teitler, M; Glennon, RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A partial agonists. J. Med. Chem., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

6977
Analogue 3: Adding Bromo at R4

4,2,3-DOB

IUPAC: 1-(4-Bromo-2,3-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: VERVNXXUCNQDRY-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-4-5-9(12)11(15-3)10(8)14-2/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69730008

Shulgin Index: See #52 DOB; Table: 5 Page: 337 Row: 27

7002
Analogue 4: Adding Methyl at R4

4-Me-2,3-DOM

IUPAC: 1-(2,3-Dimethoxy-4-methylphenyl)propan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: XVOWWIPGZCFURZ-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-6-10(7-9(2)13)12(15-4)11(8)14-3/h5-6,9H,7,13H2,1-4H3

Shulgin Index: See #60 DOM; Table: 5 Page: 338 Row: 2

7003
Analogue 5: Adding Ethyl at R4

4,2,3-DOET

IUPAC: 1-(4-Ethyl-2,3-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: PFLUZBXZLCDBOB-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-6-7-11(8-9(2)14)13(16-4)12(10)15-3/h6-7,9H,5,8,14H2,1-4H3

PubChem CID: 57486943

Shulgin Index: See #56 DOET; Table: 5 Page: 338 Row: 3

Four R5 analogues:
160
Analogue 1: Adding Methoxy at R5

TMA-4
2,3,5-Trimethoxyamphetamine

IUPAC: 1-(2,3,5-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: MJIBJXKJBRLSQA-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)7-11(15-3)12(9)16-4/h6-8H,5,13H2,1-4H3

PubChem CID: 602804; ChemSpider: 523988; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #120 TMA-4; Table: 5 Page: 339 Row: 22

See also PiHKAL: #42 Ψ-2C-T-4
#135 MMDA-3b
#136 MME
#158 TMA-2
#161 TMA-5  
See also Pharmacology notes I: p. 61, TMA-4: Subacute evaluation
p. 72, SARs

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Shulgin, AT. MMDA (MMDA-4). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 11 Apr 2003.

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

2166
Analogue 2: Adding Bromo at R5

5,2,3-DOB
5-Br-2,3-DMA
5-Bromo-2,3-dimethoxyamphetamine

IUPAC: 1-(5-Bromo-2,3-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: ZJJIBYZWBGZMEZ-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(12)6-10(14-2)11(8)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 69396115; ChemSpider: 26472392

Shulgin Index: See #52 DOB; Table: 5 Page: 339 Row: 4

See also PiHKAL: #124 META-DOB      
7057
Analogue 3: Adding Methyl at R5

5-Me-2,3-DOM

IUPAC: 1-(2,3-Dimethoxy-5-methylphenyl)propan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: QGEPUUHUMIVNBF-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-10(7-9(2)13)12(15-4)11(6-8)14-3/h5-6,9H,7,13H2,1-4H3

PubChem CID: 21932846; ChemSpider: 10687093

Shulgin Index: See #60 DOM; Table: 5 Page: 339 Row: 7

7058
Analogue 4: Adding Ethyl at R5

5,2,3-DOET

IUPAC: 1-(5-Ethyl-2,3-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: CCZARCIXJNNALJ-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-7-11(6-9(2)14)13(16-4)12(8-10)15-3/h7-9H,5-6,14H2,1-4H3

PubChem CID: 57486946

Shulgin Index: See #56 DOET; Table: 5 Page: 339 Row: 8

Five R6 analogues:
161
Analogue 1: Adding Methoxy at R6

TMA-5
2,3,6-Trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: OASZJWLOOFXASO-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13)7-9-10(14-2)5-6-11(15-3)12(9)16-4/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31013; ChemSpider: 28772; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #121 TMA-5; Table: 5 Page: 353 Row: 2

See also PiHKAL: #8 ARIADNE #42 Ψ-2C-T-4 #158 TMA-2  
See also Pharmacology notes I: p. 72, SARs
p. 97, TMA-5: Subacute evaluation

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Pirisi, MA; Nieddu, M; Burrai, L; Carta, A; Briguglio, I; Baralla, E; Demontis, MP; Varoni, MV; Boatto, G. An LC-MS-MS method for quantitative analysis of six trimethoxyamphetamine designer drugs in rat plasma, and its application to a pharmacokinetic study. Forensic Toxicol., 1 Jul 2013, 31 (2), 197–203. 305 kB. doi:10.1007/s11419-012-0177-y

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

2168
Analogue 2: Adding Bromo at R6

6,2,3-DOB
6-Br-2,3-DMA
6-Bromo-2,3-dimethoxyamphetamine

IUPAC: 1-(6-Bromo-2,3-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: OATUVSAOMSEFGM-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)6-8-9(12)4-5-10(14-2)11(8)15-3/h4-5,7H,6,13H2,1-3H3

PubChem CID: 69396333

Shulgin Index: See #52 DOB; Table: 5 Page: 352 Row: 16

See also PiHKAL: #124 META-DOB      

Maher, HM; Awad, T; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on brominated dimethoxyamphetamines: Regioisomers related to 4-Br-2,5-DMA (DOB). Drug Test. Anal., 1 Aug 2012, 4 (7–8), 591–600. 1532 kB. doi:10.1002/dta.409

Bailey, K; Gagné, DR; Pike, RK. Investigation and identification of the bromination products of dimethoxyamphetamines. J. Assoc. Off. Anal. Chem., 1 Jan 1976, 59 (5), 1162–1169. 1916 kB.

7719
Analogue 3: Adding Methyl at R6

6-Me-2,3-DOM

IUPAC: 1-(2,3-Dimethoxy-6-methylphenyl)propan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: MWSXLWTUCVALNM-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-6-11(14-3)12(15-4)10(8)7-9(2)13/h5-6,9H,7,13H2,1-4H3

Shulgin Index: See #60 DOM; Table: 5 Page: 352 Row: 19

7720
Analogue 4: Adding Ethyl at R6

6,2,3-DOET

IUPAC: 1-(6-Ethyl-2,3-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: IBAKWXIMULEKMV-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-6-7-12(15-3)13(16-4)11(10)8-9(2)14/h6-7,9H,5,8,14H2,1-4H3

PubChem CID: 57486954

Shulgin Index: See #56 DOET; Table: 5 Page: 352 Row: 20

1067
Analogue 5: Adding Iodo at R6

6-I-2,3-DMA

IUPAC: 1-(6-Iodo-2,3-dimethoxyphenyl)propan-2-amine

Formula: C11H16INO2 Molecular weight: 321.15471 g/mol InChI Key: LRJMGLDASBOPGJ-UHFFFAOYSA-N

InChI=1S/C11H16INO2/c1-7(13)6-8-9(12)4-5-10(14-2)11(8)15-3/h4-5,7H,6,13H2,1-3H3

Dawson, BA; Black, DB; Sy, W; Graham, K. 13C NMR of some iodinated methoxy-amphetamines. Magn. Reson. Chem., 1 Sep 1994, 32 (9), 557–558. 171 kB. doi:10.1002/mrc.1260320913

Seven R2,3 analogues:
275
Analogue 1: Substituting Methylenedioxy for Dimethoxy at R2,3

2,3-MDA
ORTHO-MDA
2,3-Methylenedioxyamphetamine

IUPAC: 1-(1,3-Benzodioxol-4-yl)propan-2-amine

Formula: C10H13NO2 Molecular weight: 179.21572 g/mol InChI Key: XOOVOZRNDZPGLF-UHFFFAOYSA-N

InChI=1S/C10H13NO2/c1-7(11)5-8-3-2-4-9-10(8)13-6-12-9/h2-4,7H,5-6,11H2,1H3

PubChem CID: 152655; ChemSpider: 134547; Wikipedia: 2,3-Methylenedioxyamphetamine

Shulgin Index: See #77 MDA; Table: 4 Page: 326 Row: 10

See also PiHKAL: #100 MDA      
See also TiHKAL: #28 4,5-MDO-DIPT      

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Casale, JF; Hays, PA; Klein, RFX. Synthesis and characterization of the 2,3-methylenedioxyamphetamines. J. Forensic Sci., 1 May 1995, 40 (3), 391–400. 500 kB. doi:10.1520/JFS13793J

2448
Analogue 2: Substituting Benzo for Dimethoxy at R2,3

IUPAC: 1-(Naphthalen-1-yl)propan-2-amine

Formula: C13H15N Molecular weight: 185.2649 g/mol InChI Key: ODTJDLMNBKMVGR-UHFFFAOYSA-N

InChI=1S/C13H15N/c1-10(14)9-12-7-4-6-11-5-2-3-8-13(11)12/h2-8,10H,9,14H2,1H3

PubChem CID: 413939; ChemSpider: 366505

Vilches-Herrera, M; Miranda-Sepúlveda, J; Rebolledo-Fuentes, M; Fierro, A; Lühr, S; Iturriaga-Vasquez, P; Cassels, BK; Reyes-Parada, M. Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors. Bioorg. Med. Chem., 15 Mar 2009, 17 (6), 2452–2460. 509 kB. doi:10.1016/j.bmc.2009.01.074

2447
Analogue 3: Substituting Pyrrolo[b] for Dimethoxy at R2,3

α-Me-isoT
4-IT

IUPAC: 1-(1H-Indol-4-yl)propan-2-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: FSNFARLFBCWJMF-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-8(12)7-9-3-2-4-11-10(9)5-6-13-11/h2-6,8,13H,7,12H2,1H3

PubChem CID: 55254455; ChemSpider: 26495445

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

2445
Analogue 4: Substituting Furo[b] for Dimethoxy at R2,3

4-APB

IUPAC: 1-(1-Benzofuran-4-yl)propan-2-amine

Formula: C11H13NO Molecular weight: 175.22702 g/mol InChI Key: XROLBZOMVNMIFN-UHFFFAOYSA-N

InChI=1S/C11H13NO/c1-8(12)7-9-3-2-4-11-10(9)5-6-13-11/h2-6,8H,7,12H2,1H3

PubChem CID: 10130546; ChemSpider: 8306061

Stanczuk, A; Morris, N; Gardner, EA; Kavanagh, PV. Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products. Drug Test. Anal., 1 Apr 2013, 5 (4), 270–276. 1304 kB. doi:10.1002/dta.1451

Casale, JF; Hays, PA. The characterization of 6-(2-aminopropyl)benzofuran and differentiation from its 4-, 5-, and 7-positional analogues. Microgram J., 1 Jan 2012, 9 (2), 61–74. 1652 kB.

1284
Analogue 5: Substituting Pyrrolo[d] for Dimethoxy at R2,3

7-IT

IUPAC: 1-(1H-Indol-7-yl)propan-2-amine

Formula: C11H14N2 Molecular weight: 174.24226 g/mol InChI Key: JRCRPUGDMKLCQO-UHFFFAOYSA-N

InChI=1S/C11H14N2/c1-8(12)7-10-4-2-3-9-5-6-13-11(9)10/h2-6,8,13H,7,12H2,1H3

PubChem CID: 55254240; ChemSpider: 26495376

1046
Analogue 6: Substituting 2,3-Dihydrofuro[d] for Dimethoxy at R2,3

7-APDB

IUPAC: 1-(2,3-Dihydro-1-benzofuran-7-yl)propan-2-amine

Formula: C11H15NO Molecular weight: 177.2429 g/mol InChI Key: FVHLRYWNSYCTAK-UHFFFAOYSA-N

InChI=1S/C11H15NO/c1-8(12)7-10-4-2-3-9-5-6-13-11(9)10/h2-4,8H,5-7,12H2,1H3

1040
Analogue 7: Substituting Furo[d] for Dimethoxy at R2,3

7-APB

IUPAC: 1-(1-Benzofuran-7-yl)propan-2-amine

Formula: C11H13NO Molecular weight: 175.22702 g/mol InChI Key: YVMDMFRZSDUZLK-UHFFFAOYSA-N

InChI=1S/C11H13NO/c1-8(12)7-10-4-2-3-9-5-6-13-11(9)10/h2-6,8H,7,12H2,1H3

PubChem CID: 10130548; ChemSpider: 8306063

Stanczuk, A; Morris, N; Gardner, EA; Kavanagh, PV. Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products. Drug Test. Anal., 1 Apr 2013, 5 (4), 270–276. 1304 kB. doi:10.1002/dta.1451

Casale, JF; Hays, PA. The characterization of 6-(2-aminopropyl)benzofuran and differentiation from its 4-, 5-, and 7-positional analogues. Microgram J., 1 Jan 2012, 9 (2), 61–74. 1652 kB.

Two skeleton analogues:
543
Analogue 1: With Phenylacetaldehyde skeleton

2,3-DMP2P

IUPAC: 1-(2,3-Dimethoxyphenyl)propan-2-one

Formula: C11H14O3 Molecular weight: 194.22706 g/mol InChI Key: SYYURZPSSGNDQQ-UHFFFAOYSA-N

InChI=1S/C11H14O3/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6H,7H2,1-3H3

PubChem CID: 165071; ChemSpider: 144719

Barfknecht, CF; Smith, RV; Nichols, DE; Leseney, JL; Long, JP; Engelbrecht, JA. Chemistry and pharmacological evaluation of 1-phenyl-2-propanols and 1-phenyl-2-propanones. J. Pharm. Sci., 1 May 1971, 60 (5), 799–801. 352 kB. doi:10.1002/jps.2600600533

923
Analogue 2: With 1-Benzylpiperazine skeleton

2,3-DMBZP
2,3-DMBZP

IUPAC: 1-(2,3-Dimethoxybenzyl)piperazine

Formula: C13H20N2O2 Molecular weight: 236.3101 g/mol InChI Key: RHKQXCFGQFIGNO-UHFFFAOYSA-N

InChI=1S/C13H20N2O2/c1-16-12-5-3-4-11(13(12)17-2)10-15-8-6-14-7-9-15/h3-5,14H,6-10H2,1-2H3

PubChem CID: 771965; ChemSpider: 674895

Abdel-Hay, KM; DeRuiter, J; Clark, CR. GC-MS and GC-IRD studies on the six-ring regioisomeric dimethoxybenzylpiperazines (DMBPs). Drug Test. Anal., 1 Jul 2013, 5 (7), 560–572. 985 kB. doi:10.1002/dta.1417

45 isomers:
23
Isomer 1

2C-D
LE-25
4-Methyl-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-methylphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: UNQQFDCVEMVQHM-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3

PubChem CID: 135740; ChemSpider: 119559; Drugs Forum: 2C-D; Erowid: 2C-D; Wikipedia: 2C-D

Shulgin Index: #20 2C-D; Table: 5 Page: 342 Row: 9

See also PiHKAL: #8 ARIADNE
#14 BOD
#16 BOHD
#20 2C-B
#25 3C-E
#56 DMCPA
#68 DOM
#85 GANESHA
#93 IRIS
 
See also TiHKAL: #16 4-HO-DET      
See also Pharmacology notes I: p. 94, 2C-D: Subacute evaluation
p. 175, 2C-D: Acute trials
See also Pharmacology notes II: p. 273, 2C-D
p. 280, 2C-D
p. 285, 2C-D: Report of experience
p. 310, 2C-D
p. 313, 2C-D
p. 316, 2C-D: Experiment with 2C-D

Meyer, MR; Robert, A; Maurer, HH. Toxicokinetics of novel psychoactive substances: Characterization of N-acetyltransferase (NAT) isoenzymes involved in the phase II metabolism of 2C designer drugs. Toxicol. Lett., 5 Jun 2014, 227 (2), 124–128. 693 kB. doi:10.1016/j.toxlet.2014.03.010

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Ho, B; Tansey, LW; Balster, RL; An, R; McIsaac, WM; Harris, RT. Amphetamine analogs. II. Methylated phenethylamines. J. Med. Chem., 1 Jan 1970, 13 (1), 134–135. 278 kB. doi:10.1021/jm00295a034

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. doi:10.1016/j.bmc.2008.06.009

Allred, RA. Spectral characterization of 2,4-dimethoxy-3-methylphenethylamine and comparison to 2,5-dimethoxy-4-methylphenethylamine (“2C-D”). Microgram J., 1 Jan 2005, 3 (1–2), 16–26. 107 kB.

Villalobos, CA; Bull, P; Sáez, P; Cassels, BK; Huidobro-Toro, JP. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br. J. Pharmacol., 1 Apr 2004, 141 (7), 1167–1174. 271 kB. doi:10.1038/sj.bjp.0705722

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1370 kB.

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB. doi:10.1111/j.2042-7158.1985.tb03072.x

Shulgin, AT; Carter, MF. Centrally active phenethylamines. Psychopharmacol. Commun., 1 Jan 1975, 1 (1), 93–98. 6175 kB. Rhodium.

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Meyers-Riggs, B. The alkylated 2Cs. countyourculture: rational exploration of the underground, 4 Oct 2010.

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

52
Isomer 2

DESOXY
4-Methyl-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-methylphenethylamine

IUPAC: 2-(3,5-Dimethoxy-4-methylphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: LLHRMWHYJGLIEV-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-10(13-2)6-9(4-5-12)7-11(8)14-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 44350128; ChemSpider: 21106289; Wikipedia: DESOXY

Shulgin Index: #31 DESOXY; Table: 5 Page: 349 Row: 13

Benington, F; Morin, R; Clark, LC. Mescaline analogs. X. 3,4-Dimethyl-, 3,4-dichloro- and 3,5-dimethoxy-4-methyl-β-phenethylamines. J. Org. Chem., 1 Nov 1960, 25 (11), 2066–2067. 286 kB. doi:10.1021/jo01081a626

53
Isomer 3

2,4-DMA
2,4-Dimethoxyamphetamine

IUPAC: 1-(2,4-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: DQWOZMUBHQPFFF-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)7-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3

PubChem CID: 417604; ChemSpider: 124411; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #35 2,4-DMA; Table: 4 Page: 327 Row: 11

See also PiHKAL: #55 3,4-DMA #124 META-DOB #157 TMA  
See also Pharmacology notes I: p. 144, 2,4-DMA

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

54
Isomer 4

2,5-DMA
DMA
DOH
2,5-Dimethoxyamphetamine

IUPAC: 1-(2,5-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: LATVFYDIBMDBSY-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3

PubChem CID: 62787; ChemSpider: 56526; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #38 DMA; Table: 4 Page: 330 Row: 17, #36 2,5-DMA; Table: 4 Page: 335 Row: 22

See also PiHKAL: #55 3,4-DMA
#62 DOB
#64 DOC
#67 DOI
#90 IDNNA
#124 META-DOB
#126 METHYL-DMA
See also Pharmacology notes I: p. 57, 2,5-DMA: Subacute evaluation
p. 58, 2,5-DMA: Subjective response
See also Pharmacology notes II: p. 276, 2,5-DMA

Fenderson5555. Shulgin’s syntheses of 2,5-DMA, DOB and DOEF. 5 Dec 2011.

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Shulgin, AT; Dyer, DC. Psychotomimetic phenylisopropylamines. 5. 4-Alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem., 1 Jan 1975, 18 (12), 1201–1204. 534 kB. doi:10.1021/jm00246a006

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1188 kB. doi:10.1021/jm00256a016

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Glennon, RA; Bondarev, ML; Khorana, N; Young, R. β-Oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 2004, 47 (24), 6034–6041. 146 kB. doi:10.1021/jm040082s

Runyon, SP; Mosier, PD; Roth, BL; Glennon, RA; Westkaemper, RB. Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: A ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation. J. Med. Chem., 2008, 51 (21), 6808–2828. 2229 kB. doi:10.1021/jm800771x

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT2A and 5-HT2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. doi:10.1038/sj.bjp.0704747

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1992, 22 (12), 1383–1394. 765 kB. doi:10.3109/00498259209056689

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, X. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. J. Med. Chem., 1 Jan 1991, 34 (1), 276–281. 833 kB. doi:10.1021/jm00105a043

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. doi:10.1007/s11419-008-0041-2

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Dyer, DC; Nichols, DE; Rusterholz, DB; Barfknecht, CF. Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines. Life Sci., 1 Oct 1973, 13 (7), 885–896. 398 kB. doi:10.1016/0024-3205(73)90079-9

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. doi:10.1016/0024-3205(77)90099-6

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Glennon, RA; Young, R; Rosecrans, JA. A comparison of the behavioral effects of DOM homologs. Pharmacol. Biochem. Behav., 1 Apr 1982, 16 (4), 557–559. 256 kB. doi:10.1016/0091-3057(82)90414-2

Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4445 kB. doi:10.1021/bk-1989-0413.ch018

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

55
Isomer 5

3,4-DMA
DMA
3,4-Dimethoxyamphetamine

IUPAC: 1-(3,4-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: KAZPHAGSWZTKDW-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3

PubChem CID: 8423; ChemSpider: 8116; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #38 DMA; Table: 4 Page: 330 Row: 17

See also PiHKAL: #53 2,4-DMA #124 META-DOB #157 TMA  
See also Pharmacology notes I: p. 143, 3,4-DMA

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

Butterick, JR; Unrau, AM. Studies on theoretical psychotogens. Synthesis of O-methylated analogs of catecholamine neurotransmitters and metabolic precursors. Can. J. Chem., 1 Jan 1974, 52 (16), 2873–2879. 305 kB. doi:10.1139/v74-418

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Barfknecht, CF; Nichols, DE. Effects of S-(+)- and R-(-)-3,4,dimethoxyphenylisopropylamines in the rat. J. Med. Chem., 1 Jan 1972, 15 (1), 109–110. 295 kB. doi:10.1021/jm00271a037

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. doi:10.1007/978-1-4757-0510-2_6 Rhodium.

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. doi:10.1016/j.bmc.2003.10.027

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

123
Isomer 6

MEPEA
3-Methoxy-4-ethoxyphenethylamine

IUPAC: 2-(4-Ethoxy-3-methoxyphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: AFMUTJRFLRYILG-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-14-10-5-4-9(6-7-12)8-11(10)13-2/h4-5,8H,3,6-7,12H2,1-2H3

PubChem CID: 142076; ChemSpider: 125332; Wikipedia: 3-Methoxy-4-ethoxyphenethylamine

Shulgin Index: #90 MEPEA; Table: 4 Page: 330 Row: 32

See also PiHKAL: #55 3,4-DMA      

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

2045
Isomer 7

3,5-DMA
3,5-Dimethoxyamphetamine

IUPAC: 1-(3,5-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: PDCLPGSYMZLLDX-UHFFFAOYSA-N Properties: Essential amphetamine and Quasi-essential amphetamine

InChI=1S/C11H17NO2/c1-8(12)4-9-5-10(13-2)7-11(6-9)14-3/h5-8H,4,12H2,1-3H3

PubChem CID: 91247; ChemSpider: 82397

Shulgin Index: #39 3,5-DMA; Table: 4 Page: 336 Row: 28

See also PiHKAL: #55 3,4-DMA #124 META-DOB #157 TMA  

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. doi:10.1021/jm00295a007

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

2163
Isomer 8

2,6-DMA
2,6-Dimethoxyamphetamine

IUPAC: 1-(2,6-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: OHGNLLDQBKOWJW-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)7-9-10(13-2)5-4-6-11(9)14-3/h4-6,8H,7,12H2,1-3H3

PubChem CID: 141048; ChemSpider: 124412

Shulgin Index: #37 2,6-DMA; Table: 4 Page: 337 Row: 23

See also PiHKAL: #55 3,4-DMA #124 META-DOB    

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. doi:10.1002/omr.1270210611

Antun, F; Smythies, JR; Benington, F; Morin, RD; Barfknecht, CF; Nichols, DE. Native fluorescence and hallucinogenic potency of some amphetamines. Experientia, 15 Jan 1971, 27 (1), 62–63. 248 kB. doi:10.1007/BF02137743

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

2209
Isomer 9

MM-GEA
3-Methoxy-N,N-dimethyltyramine
4-Hydroxy-3-methoxy-N,N-dimethylphenethylamine

IUPAC: 4-[2-(Dimethylamino)ethyl]-2-methoxyphenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: SQKKYSLRUHVTFX-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C11H17NO2/c1-12(2)7-6-9-4-5-10(13)11(8-9)14-3/h4-5,8,13H,6-7H2,1-3H3

PubChem CID: 161861; ChemSpider: 142157

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 5

Pummangura, S; McLaughlin, JL; Schifferdecker, RC. Cactus alkaloids. XLVII. β-Phenethylamines from the “Missouri Pincushion”, Coryphantha (Neobessya) missouriensis. J. Nat. Prod., 1 Jan 1981, 44 (5), 614–616. 261 kB. doi:10.1021/np50017a022

5390
Isomer 10

N-Me-2,5-DMPEA
25H-NMe
2,5-Dimethoxy-N-methylphenethylamine

IUPAC: 2-(2,5-Dimethoxyphenyl)-N-methylethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: PIGIFXLLTQEIPK-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12-7-6-9-8-10(13-2)4-5-11(9)14-3/h4-5,8,12H,6-7H2,1-3H3

PubChem CID: 83098; ChemSpider: 74968

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 8

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol. Pharmacol., 1 Jan 2006, 70 (6), 1956–1964. 361 kB. doi:10.1124/mol.106.028720

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

2175
Isomer 11

2,5-MH-MMA
5-Hydroxy-2-methoxy-N-methylamphetamine

IUPAC: 4-Methoxy-3-[2-(methylamino)propyl]phenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: MJHSFKIGFVIAFL-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12-2)6-9-7-10(13)4-5-11(9)14-3/h4-5,7-8,12-13H,6H2,1-3H3

PubChem CID: 179091; ChemSpider: 155883

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 334 Row: 26

See also PiHKAL: #126 METHYL-DMA      

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

344
Isomer 12

2-DES-Me-DOM
2-DM-DOM
2-Hydroxy-5-methoxy-4-methylamphetamine

IUPAC: 2-(2-Aminopropyl)-4-methoxy-5-methylphenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: NIRJHEFWNFTPAN-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-7-4-10(13)9(5-8(2)12)6-11(7)14-3/h4,6,8,13H,5,12H2,1-3H3

PubChem CID: 12611596; ChemSpider: 23242115

Shulgin Index: See #60 DOM; Table: 5 Page: 342 Row: 8

Eckler, JR; Chang-Fong, J; Rabin, RA; Smith, C; Teitler, M; Glennon, RA; Winter, JC. Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM. Pharmacol. Biochem. Behav., 1 Jan 2003, 75 (4), 845–852. 294 kB. doi:10.1016/S0091-3057(03)00159-X

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Eckler, JR. Stimulus control by hallucinogens: SSRI interactions. Ph. D. Thesis, State University of New York, Buffalo, NY, USA, 20 Dec 2002. 2879 kB.

345
Isomer 13

5-DES-Me-DOM
5-DM-DOM
5-Hydroxy-2-methoxy-4-methylamphetamine

IUPAC: 5-(2-Aminopropyl)-4-methoxy-2-methylphenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: UVEGZSXIBVSOJB-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-7-4-11(14-3)9(5-8(2)12)6-10(7)13/h4,6,8,13H,5,12H2,1-3H3

PubChem CID: 44385952; ChemSpider: 23241852

Shulgin Index: See #60 DOM; Table: 5 Page: 340 Row: 10

Eckler, JR; Chang-Fong, J; Rabin, RA; Smith, C; Teitler, M; Glennon, RA; Winter, JC. Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM. Pharmacol. Biochem. Behav., 1 Jan 2003, 75 (4), 845–852. 294 kB. doi:10.1016/S0091-3057(03)00159-X

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Eckler, JR. Stimulus control by hallucinogens: SSRI interactions. Ph. D. Thesis, State University of New York, Buffalo, NY, USA, 20 Dec 2002. 2879 kB.

376
Isomer 14

4-Me-2,6-DMPEA
Ψ-2C-D
2,6-Dimethoxy-4-methylphenethylamine

IUPAC: 2-(2,6-Dimethoxy-4-methylphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: SZSNDXVVDYACMG-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-6-10(13-2)9(4-5-12)11(7-8)14-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 55253624; ChemSpider: 26492871

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 17

See also PiHKAL: #162 TMA-6      
2407
Isomer 15

β,4-Dimethoxyamphetamine

IUPAC: 1-Methoxy-1-(4-methoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: WHPCVJVNMYMZAG-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)11(14-3)9-4-6-10(13-2)7-5-9/h4-8,11H,12H2,1-3H3

PubChem CID: 45091547; ChemSpider: 24205436

2397
Isomer 16

4-Ethoxynorephedrine

IUPAC: 2-Amino-1-(4-ethoxyphenyl)propan-1-ol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: FMLOYSDSTNHJOH-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-14-10-6-4-9(5-7-10)11(13)8(2)12/h4-8,11,13H,3,12H2,1-2H3

PubChem CID: 43209106; ChemSpider: 24205416

6169
Isomer 17

BO3MM

IUPAC: 2-Methoxy-2-(3-methoxyphenyl)-N-methylethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: OYKAQMUUZGTZBP-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12-8-11(14-3)9-5-4-6-10(7-9)13-2/h4-7,11-12H,8H2,1-3H3

PubChem CID: 53276192

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 19

6171
Isomer 18

BO3ME

IUPAC: 2-Ethoxy-2-(3-methoxyphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: MZYKODQKQQGHBI-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-14-11(8-12)9-5-4-6-10(7-9)13-2/h4-7,11H,3,8,12H2,1-2H3

PubChem CID: 53276153

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 21

6174
Isomer 19

BO3MA

IUPAC: 1-Methoxy-1-(3-methoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: FQEDVOPIXYOVTK-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)11(14-3)9-5-4-6-10(7-9)13-2/h4-8,11H,12H2,1-3H3

PubChem CID: 61619297; ChemSpider: 27963017

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 24

6201
Isomer 20

BO3E

IUPAC: 2-(3-Ethoxyphenyl)-2-methoxyethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: YTFUARKRGLLGBK-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-14-10-6-4-5-9(7-10)11(8-12)13-2/h4-7,11H,3,8,12H2,1-2H3

PubChem CID: 65438932

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 322 Row: 1

6378
Isomer 21

N-Me-DMPEA-2

IUPAC: 2-(2,3-Dimethoxyphenyl)-N-methylethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: HRZVUFHEZZHTEN-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12-8-7-9-5-4-6-10(13-2)11(9)14-3/h4-6,12H,7-8H2,1-3H3

PubChem CID: 202629; ChemSpider: 175456

Shulgin Index: See #46 2,3-DMPEA; Table: 4 Page: 325 Row: 28

6402
Isomer 22

2,3-EMPEA

IUPAC: 2-(2-Ethoxy-3-methoxyphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: ZAFQGFANJDACBB-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-14-11-9(7-8-12)5-4-6-10(11)13-2/h4-6H,3,7-8,12H2,1-2H3

PubChem CID: 4715424; ChemSpider: 3902730

Shulgin Index: See #46 2,3-DMPEA; Table: 4 Page: 326 Row: 2

6460
Isomer 23

N-Me-DMPEA-3

IUPAC: 2-(2,4-Dimethoxyphenyl)-N-methylethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: WEDBJHQKLMPQQT-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12-7-6-9-4-5-10(13-2)8-11(9)14-3/h4-5,8,12H,6-7H2,1-3H3

PubChem CID: 202631; ChemSpider: 175458

Shulgin Index: See #47 2,4-DMPEA; Table: 4 Page: 327 Row: 10

6466
Isomer 24

2,4-EMPEA

IUPAC: 2-(2-Ethoxy-4-methoxyphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: QAXUKBWYVGIBRW-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-14-11-8-10(13-2)5-4-9(11)6-7-12/h4-5,8H,3,6-7,12H2,1-2H3

PubChem CID: 22682788; ChemSpider: 20503026

Shulgin Index: See #35 2,4-DMA; Table: 4 Page: 327 Row: 16

6513
Isomer 25

Coryneine

IUPAC: 2-(3,4-Dihydroxyphenyl)-N,N,N-trimethylethanaminium

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: VDTBORSEFUUDTP-UHFFFAOYSA-O

InChI=1S/C11H17NO2/c1-12(2,3)7-6-9-4-5-10(13)11(14)8-9/h4-5,8H,6-7H2,1-3H3,(H-,13,14)/p+1

PubChem CID: 165581; ChemSpider: 145116

Shulgin Index: See #49 DMPEA; Table: 4 Page: 328 Row: 13

6530
Isomer 26

N,N-Me-DHA

IUPAC: 4-[2-(Dimethylamino)propyl]benzene-1,2-diol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: IGATVIFAMZLMSA-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12(2)3)6-9-4-5-10(13)11(14)7-9/h4-5,7-8,13-14H,6H2,1-3H3

PubChem CID: 21151685

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 30

6534
Isomer 27

DHEA

IUPAC: 4-[2-(Ethylamino)propyl]benzene-1,2-diol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: CKUGRMSDBDIJRN-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-12-8(2)6-9-4-5-10(13)11(14)7-9/h4-5,7-8,12-14H,3,6H2,1-2H3

PubChem CID: 130357; ChemSpider: 115342

Shulgin Index: See #33 DHA; Table: 4 Page: 328 Row: 34

6564
Isomer 28

MHMA

IUPAC: 2-Methoxy-4-[2-(methylamino)propyl]phenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: UVDWYWYWOMOEFX-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12-2)6-9-4-5-10(13)11(7-9)14-3/h4-5,7-8,12-13H,6H2,1-3H3

PubChem CID: 3081137; ChemSpider: 2338803

Shulgin Index: See #94 MHA; Table: 4 Page: 329 Row: 14

6568
Isomer 29

MH-α-Et-PEA

IUPAC: 4-(2-Aminobutyl)-2-methoxyphenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: XTTYRSUNCGHTHB-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-9(12)6-8-4-5-10(13)11(7-8)14-2/h4-5,7,9,13H,3,6,12H2,1-2H3

PubChem CID: 20229534

Shulgin Index: See #33 DHA; Table: 4 Page: 329 Row: 18

6603
Isomer 30

HMMA

IUPAC: 2-Methoxy-5-[2-(methylamino)propyl]phenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: DRQIXEJQEHDMDV-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12-2)6-9-4-5-11(14-3)10(13)7-9/h4-5,7-8,12-13H,6H2,1-3H3

PubChem CID: 18620432; ChemSpider: 13310118

Shulgin Index: See #33 DHA; Table: 4 Page: 330 Row: 3

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Torre, R; Farré, M. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharmacol. Sci., 1 Oct 2004, 25 (10), 505–508. 104 kB. doi:10.1016/j.tips.2004.08.001

6606
Isomer 31

β-Me-DMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)propan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: RRARQHPQZWUMFW-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(7-12)9-4-5-10(13-2)11(6-9)14-3/h4-6,8H,7,12H2,1-3H3

PubChem CID: 171416; ChemSpider: 149855

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 6

6614
Isomer 32

N-Me-DMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-N-methylethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: HNJWKRMESUMDQE-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12-7-6-9-4-5-10(13-2)11(8-9)14-3/h4-5,8,12H,6-7H2,1-3H3

PubChem CID: 77039; ChemSpider: 69485

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 14

6628
Isomer 33

EMPEA

IUPAC: 2-(3-Ethoxy-4-methoxyphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: NJVDYCNYTDOXPX-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-3-14-11-8-9(6-7-12)4-5-10(11)13-2/h4-5,8H,3,6-7,12H2,1-2H3

PubChem CID: 145108; ChemSpider: 128021

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 28

6817
Isomer 34

β,2-HO-5,N-DMeA

IUPAC: 2-[1-Hydroxy-2-(methylamino)propyl]-4-methylphenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: NIFPLZBHXVSTJP-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-7-4-5-10(13)9(6-7)11(14)8(2)12-3/h4-6,8,11-14H,1-3H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 334 Row: 17

6819
Isomer 35

β-HO-N-Me-2-M-5-MePEA

IUPAC: 1-(2-Methoxy-5-methylphenyl)-2-(methylamino)ethanol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: QFJRJKAFEPKJME-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-4-5-11(14-3)9(6-8)10(13)7-12-2/h4-6,10,12-13H,7H2,1-3H3

PubChem CID: 60904268; ChemSpider: 25665979

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 19

6820
Isomer 36

β-HO-2-M-5-MeA

IUPAC: 2-Amino-1-(2-methoxy-5-methylphenyl)propan-1-ol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: TZOQRNSNVWMTCO-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-7-4-5-10(14-3)9(6-7)11(13)8(2)12/h4-6,8,11,13H,12H2,1-3H3

PubChem CID: 56333; ChemSpider: 50834

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 334 Row: 20

6830
Isomer 37

N,N-Me-2,5-HMPEA

IUPAC: 2-[2-(Dimethylamino)ethyl]-4-methoxyphenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: QJJXVGKAMLYOCJ-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12(2)7-6-9-8-10(14-3)4-5-11(9)13/h4-5,8,13H,6-7H2,1-3H3

PubChem CID: 12611617; ChemSpider: 23241701

Shulgin Index: See #22 2C-H; Table: 4 Page: 334 Row: 30

6860
Isomer 38

β-Me-2,5-DMPEA

IUPAC: 2-(2,5-Dimethoxyphenyl)propan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: MWCQGGZRKWDESA-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(7-12)10-6-9(13-2)4-5-11(10)14-3/h4-6,8H,7,12H2,1-3H3

PubChem CID: 202668; ChemSpider: 175495

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 10

6923
Isomer 39

N-Me-3,5-DMPEA

IUPAC: 2-(3,5-Dimethoxyphenyl)-N-methylethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: NCSUFYPUXBKLQA-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12-5-4-9-6-10(13-2)8-11(7-9)14-3/h6-8,12H,4-5H2,1-3H3

PubChem CID: 12866444; ChemSpider: 14025824

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 23

6969
Isomer 40

N-Me-2,6-DMPEA

IUPAC: 2-(2,6-Dimethoxyphenyl)-N-methylethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: UIJWLWCOVQFZHF-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-12-8-7-9-10(13-2)5-4-6-11(9)14-3/h4-6,12H,7-8H2,1-3H3

PubChem CID: 15211438

Shulgin Index: See #48 2,6-DMPEA; Table: 4 Page: 337 Row: 19

7760
Isomer 41

6-Me-2,4-DMPEA

IUPAC: 2-(2,4-Dimethoxy-6-methylphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: FHWABNSNUFDILS-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-6-9(13-2)7-11(14-3)10(8)4-5-12/h6-7H,4-5,12H2,1-3H3

PubChem CID: 55266219; ChemSpider: 26471861

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 10

2578
Isomer 42

iso-2C-D

IUPAC: 2-(2,4-Dimethoxy-3-methylphenyl)ethan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: OOORAHFIUDETAY-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8-10(13-2)5-4-9(6-7-12)11(8)14-3/h4-5H,6-7,12H2,1-3H3

Allred, RA. Spectral characterization of 2,4-dimethoxy-3-methylphenethylamine and comparison to 2,5-dimethoxy-4-methylphenethylamine (“2C-D”). Microgram J., 1 Jan 2005, 3 (1–2), 16–26. 107 kB.

2760
Isomer 43

IUPAC: 2-Methoxy-3-[2-(methylamino)propyl]phenol

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: IUYNSRBNRQIZHF-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12-2)7-9-5-4-6-10(13)11(9)14-3/h4-6,8,12-13H,7H2,1-3H3

Geertsen, S; Foster, BC; Cyr, DLWTD; Casley, W. Metabolism of methoxyphenamine and 2-methoxyamphetamine inP4502D6-transfected cells and cell preparations. Xenobiotica, 1995, 25 (9), 895–906. 731 kB. doi:10.3109/00498259509046661

702
Isomer 44

homo-3,4-DMPEA

IUPAC: 3-(3,4-Dimethoxyphenyl)propan-1-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: WYYQSKUMIFPNFW-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-13-10-6-5-9(4-3-7-12)8-11(10)14-2/h5-6,8H,3-4,7,12H2,1-2H3

Benington, F; Morin, RD; Clark, LC. Mescaline analogs. VI. Mescaline homologs. J. Org. Chem., 1 Dec 1956, 21 (12), 1545–1546. 282 kB. doi:10.1021/jo01118a635

1088
Isomer 45

N-MeO-PMA
N,4-Dimethoxyamphetamine

IUPAC: N-Methoxy-1-(4-methoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: YJTVYMPUXRXEER-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-9(12-14-3)8-10-4-6-11(13-2)7-5-10/h4-7,9,12H,8H2,1-3H3

Benington, F; Morin, RD; Clark, LC. Behavioral and neuropharmacological actions of N-aralkylhydroxylamines and their O-methyl ethers. J. Med. Chem., 1 Jan 1965, 8 (1), 100–104. 634 kB. doi:10.1021/jm00325a020

Show all 76 analogues and isomers Show only the one N analogues Show only the two α analogues Show only the one R2 analogues Show only the four R3 analogues Show only the five R4 analogues Show only the four R5 analogues Show only the five R6 analogues Show only the seven R2,3 analogues Show only the two skeleton analogues
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